Conventional political wisdom in the bellwether state of Florida has always
focused on Cuban-Americans, especially those influential exiles who take a
hard line against any U.S. engagement with Fidel Castro's Cuba. Cross them,
says the presidential candidate handbook, and say adios to the Sunshine
State's 27 electoral votes.

So why would Barack Obama  who is scraping to keep up with Hillary Clinton
for the 2008 Democratic presidential nomination  ignore that seemingly
golden rule? Why, in a Tuesday op-ed piece in the Miami Herald, would he challenge
the Cuban-American elders and call for dismantling President Bush's hefty
restrictions on Cuban-Americans making visits and sending money to relatives
in Cuba?

Maybe it's because Obama knows a new conventional wisdom may well be taking
shape in the state  one that could actually make his declarations this
week an asset when Florida holds its primary election next January. "A
democratic opening in Cuba is, and should be, the foremost objective of our
policy," Obama wrote in the Herald. But while making that standard
declaration, he also argued that "Cuban-American connections to family in
Cuba are not only a basic right in humanitarian terms, but also our best tool for
helping to foster the beginnings of grassroots democracy on the island." As
a result, he said, "I will grant Cuban-Americans unrestricted rights to visit
family and send remittances to the island."

The restrictions  widely viewed as a thank-you to the hardline exile bloc
that helped Bush win Florida in 2000  allow Cuban-Americans to visit the
island for only 14 days every three years and limit remittances to $1,200
per year. "It's almost as if you have to decide ahead of time when a relative is
going to die," says Miami immigration attorney Magda Montiel Davis, a
Cuban-American moderate who says she is now voting for Obama after reading
his Herald article. Bush and hard-line leaders insist the policy helps keep U.S. dollars out of Castro's hands. But "it has also made [Cubans
living in Cuba] more dependent on the Castro regime," Obama argued in the
Herald, "and isolated them from the transformative message carried there by
Cuban-Americans."

In response to Obama's statement, Hillary Clinton continued her recent attacks on
his perceived foreign policy naivete, insisting that "until it is clear what
type of policies might come with a new [Cuban] government, we cannot talk about
changes in the U.S. policies toward Cuba." But by playing that safe card in
Florida, Clinton may have allowed herself to be "outmaneuvered by Obama on
this one," says one Cuban-American leader who asked not to be identified, pointing to a
recent Florida International University poll showing that more than 55% of
Cuban-Americans in Miami favor unrestricted travel to Cuba.

That survey, say academics like Rafael Lima, a University of Miami
communications professor and the son of an exile once imprisoned by Castro,
reflects the growing number of younger, more moderate Cuban-American voters
in South Florida  and the waning clout of the older, more conservative
generation. Unlike their elders, the younger generation believes that the
45-year-old economic embargo against Cuba has utterly failed to dislodge its
communist leader. As a result, Obama could now galvanize those moderates,
who Lima says "have been waiting for a viable presidential candidate to wave
their banner for once."

Not that Miami's Cuban-American community has an overwhelming number of
registered Democrats to woo in the first place. The exiles have
traditionally voted Republican ever since they abandoned President John F. Kennedy because
of his botched direction of the Bay of Pigs invasion in 1961. But Miami
Democrats like Elena Freyre, a Cuban-American art gallery owner in Little
Havana, say they've been trying to tell Democratic candidates to stop
parroting the hard-line position. "Obama's people were the first who ever
said to me on the phone, ‘Wait, let me get a pen and write that down,'" says
Freyre. "He's the first to have the cojones to say Bush's policy is wrong,
and I think it's going to wake up a lot of moderate Cuban-American voters."

At the same time, Obama's stance could help him garner a larger share of the
state's non-Cuban Democrats (especially non-Cuban Latinos), who were
repulsed by hard-line exile politics during the Elian Gonzalez fiasco. And as for the
general election, even many hard-line voters have changed their mind about
Bush's travel and remittance policy.

Obama will get a better idea of how his position is playing out
when he takes the stage Saturday for a Miami Democratic fundraiser at the Miami-Dade County Auditorium  located in the hard-line bastion of Little Havana. He and
Clinton will also get a chance to square off on Cuba policy on Sept. 9 during a
scheduled Democratic presidential debate at the University of Miami. The
responses at both events should be a good gauge of whether the rules in
Florida are really ready to be broken.

The original version of this story inaccurately stated that the Democratic presidential debate at the University of Miami was scheduled for Sept. 30. It is scheduled for Sept. 9.